This is the second installment in a series, “Battle Tested,” that analyzes early campaigns run by some Democrats seeking the presidential nomination. For our first story, on Sen. Kirsten Gillibrand, click here.

When New Jersey Sen. Cory Booker talks about defeating President Donald Trump, he often alludes to another political battle.

“When it comes to what is going to be one of America’s more important prize fights, this won’t be the first time I had to put on the gloves and fight a significant difficult, hard, bruising battle,” Booker told CQ Roll Call.

“I showed that you can actually fight and win, but not stoop to the levels and tactics and dirty tricks of the opposition.”

That original opposition was two decades ago, against the political machine of Sharpe James, the five-term Newark mayor who later served time in federal prison on fraud charges.

Booker never actually defeated James himself. But he went up against James’ machine several times, first when he won a city council race and again when he challenged James directly in 2002 and lost. The ugliness of that race has become part of Booker’s political lore — so much so that he name-dropped “Street Fight,” the Oscar-nominated documentary about it, at a CNN town hall earlier this year.

Booker was elected to the Senate in a 2013 special election. He easily won a full term in 2014. But ever since he started running in Newark, his critics have said he was really running for president. They argue his superhero acts — running into a burning house to save a woman, shoveling a resident’s driveway — were good for his national profile, but less so for a city that needed better management.

Now that he is actually running for president, Booker is polling at 1 percent in Iowa. But he’s building a deep organization in the state.

“He’s not letting polls dictate his actions,” said former Newark City Councilman Ron C. Rice. “He’s building a grassroots local army of folks quietly, under the radar.”

That strategy is reminiscent of Booker’s first campaigns in Newark, New Jersey’s largest city, when he wore out pairs of shoes knocking on doors. Those early races also reflect the complicated relationship Booker, who grew up in an upscale North Jersey suburb, has with his adopted hometown — and the questions about authenticity he continues to confront on the national stage.

[jwp-video n=”1″]

The impressive win

Booker’s pedigree and connections have always been a double-edged sword in Newark, where the poverty rate is nearly 30 percent. They’ve helped him bring investment to the city, but underscored that he was from somewhere else. Booker’s parents were IBM executives who broke the race barrier to move into a white suburb. 

With a degree from Stanford and a Rhodes scholarship under his belt, Booker began driving down to Newark to work as a tenant advocate during his second year of law school at Yale. He eventually moved into the Central Ward, the epicenter of the 1967 riots that left the city without a grocery store for 40 years.

Two years after he arrived, Booker ran in the 1998 city council election against George Branch, a former professional boxer who had represented the Central Ward for 16 years. But in a city driven by machine politics, he was really running against James, who saw the newcomer as a threat. 

“The race I’m running now reminds me of 1998 more than any of my races,” Booker said. “We were terribly underestimated” and facing “a lot of rhetoric and attacks that you see Donald Trump using.” 

Booker’s most impressive victory almost didn’t happen. Branch finished first, 340 votes ahead of him. The contest went to a runoff, however, because Branch didn’t surpass 50 percent of the vote.

As he would continue to do in future races, Booker outraised his opponent, raking in money from outside Newark from the likes of Barbra Streisand. He also invested heavily in retail politics.

“He just grinded it out,” campaign manager Bill Crawley recalled. “We would go to Stella Wright, and he would knock on those doors two, three times,” Crawley said, referring to one of the major low-income housing developments in the Central Ward.

After turning out voters in the projects who had never voted before, Booker won the runoff 55 percent to 45 percent.

“For Cory Booker to beat George Branch in an all-African American area as an outsider was a tremendous feat,” said councilman Augusto Amador, who won his seat the same year as Booker.

“We knew that there was only one way we were going to win that election,” Booker said. “Our pathway in this election is similar, which is to out-organize in the grassroots.”

But that 1998 race was just a warmup for his next campaign, when the machine no longer underestimated him. 

[jwp-video n=”2″]

The ‘Street Fight’

When Booker, then 32, announced his campaign against James, who was more than twice his age, he was challenging the most powerful African American politician in the state. He called for a “renaissance for the rest of us,” arguing that the development James had brought to the city had not benefited the city’s poorest residents.

“The thinking was that [Newark] didn’t need just a recycled person from the political class; it needed a kick from the outside, and Cory was that kick,” said Rice, who ran for council on Booker’s slate.

But unlike Branch, James had the firepower to weaponize Booker’s outsider status.

Booker was living in Brick Towers, a low-income high rise in the Central Ward. James argued that Booker didn’t live in Newark — a claim he repeated to CQ Roll Call last week. During the race, James also insinuated that Booker was actually Jewish and that he was a puppet of the Republican Party and the Ku Klux Klan.

“I won because I was the real deal, and he was a carpetbagger,” James said.

James played into the anxieties of an African American community that felt it had been abandoned after the riots.

“To me, it’s the difference between home rule and foreign domination,” Newark playwright and poet Amiri Baraka, the father of the current mayor, told The Star-Ledger in late April 2002.

The state’s Democratic establishment was with James, including the governor, the congressional delegation and almost every union. Booker’s only support within the city power structure was from the firefighters’ union, which was upset with their contract negotiations.

“Any business that put our signs up — they were raided by code enforcement. It was a lot to overcome,” Booker campaign manager Pablo Fonseca said.

Just two weeks before the election, Booker went negative. His TV spots called out James for driving a Rolls Royce, owning a yacht and taking a $200,000 salary.

As he had in the city council race and as he’s doing now in Iowa, Booker prioritized retail politics. But the mayor’s strength in his home South Ward dwarfed Booker’s victories in the North and East wards. Booker lost by 7 points.

“Cory was a councilman of a ward and Sharpe James was the name you knew,” Rice said.

[jwp-video n=”3″]

Take two

Booker was determined to become the name Newark residents knew and almost immediately started campaigning for the 2006 mayoral race.

Several factors made that race different. Booker’s decision to stay in Newark after his 2002 loss helped prove his commitment to the city. James was growing older and his ethical baggage was building. One of his top aides switched to Booker’s team midway through his fifth term.

Booker had learned from his 2002 race too and was faster to answer the attacks.

“He is a much tougher candidate,” said media consultant Brad Lawrence, who worked against Booker in 2002 but switched sides in 2006 and has been with him on every race since.

“Whatever naiveté existed in 2002, I think he understands how much you have to fight,” Lawrence said.

In the end, James didn’t even run, dropping out without enough time for anyone else to mount a serious campaign.

“Mr. James saw the writing on the wall,” said Amador, the councilman who had been with the mayor in 2002, but backed Booker in 2006.

“The establishment came onboard,” said Rice, who was again running on Booker’s city council slate and backed Booker over his own father, then the deputy mayor. “They didn’t have a choice, right? Either roll with us, or we’re going to roll over you.”

Booker ended up easily defeating Ronald L. Rice, who had a tepid endorsement from James.

Running for president

When he launched his presidential bid this year, Booker had the backing of his state’s entire congressional delegation. But not everyone thinks he did right by Newark.

“Like many people in Newark, we were ready for change,” said longtime resident Bill Chappel, who supported Booker’s city council run in 1998. “As we say now in Newark, we drank the Cory Booker Kool-Aid.”

“I have mixed feelings,” said Amador, who’s endorsed Booker for president. “I like Cory, but there were some things that left a bitter taste in my mouth when he was mayor of the city of Newark.”

Having investigated rampant corruption at the agency overseeing the city’s water system, which occurred under Booker’s watch, Amador has concerns about the way Booker managed the city.

“He was campaigning for president; he wasn’t campaigning for mayor,” said Columbia economics professor Brendan O’Flaherty, the acting chief financial officer of Newark during the first summer of Booker’s administration. Booker became a “celebrity mayor,” he’s written, while the city was saddled with rising crime, a large deficit and the water system scandal.  

On the presidential campaign trail, Booker’s appeal for unity and love — sometimes dismissed as inauthentic and corny — is part of his strategy to inspire a “movement election.”

“That’s going to be how we’re going to win not just the primary, but it’s how we’re going to beat Donald Trump,” he said. 

Even James, who blames Booker for his 2008 fraud conviction and favors former vice president Joe Biden in the primary, isn’t saying no to voting for him.

“If he wins the primary, I’ll support him for president. He’ll bring prestige and visibility to the city of Newark that truly needs it,” he said.

“And maybe I get to carry his bag for a couple of trips.”